Hydrochloric Acid → methyl (1S,2S)-1-({[(1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl]amino}carbonyl)-2-methylbutylcarbamate

HRID 1174139Notes

Reaction equation

HRID 1174139 reaction equation
[CH2:1]([C@H:8]([NH:28][C:29]([C@@H:31]([NH:36][C:37](=[O:40])[O:38][CH3:39])[C@@H:32]([CH3:35])[CH2:33][CH3:34])=[O:30])[C@@H:9]([OH:27])[CH2:10][C@@H:11]([NH:19]C(OC(C)(C)C)=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[NH2:19][C@@H:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:10][C@H:9]([OH:27])[C@@H:8]([NH:28][C:29]([C@@H:31]([NH:36][C:37](=[O:40])[O:38][CH3:39])[C@@H:32]([CH3:35])[CH2:33][CH3:34])=[O:30])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86726174methyl (1S,2S)-1-[({(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-phenylpentyl}amino)carbonyl]-2-methylbutylcarbamate

Product 1

HCID 86726173methyl (1S,2S)-1-({[(1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl]amino}carbonyl)-2-methylbutylcarbamateYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution containing the crude product from Example 9A in THF (150 mL) was treated with an HCl solution (5 mL, 4 N in dioxane), and the mixture was heated at 60° C. for 2 hours, cooled to 25° C. and concentrated. The concentrate was partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to give the title compound (0.36 g, 61% yield).

Workup

  1. temperaturecooled to 25° C.
  2. concentrationconcentrated
  3. customThe concentrate was partitioned between ethyl acetate and saturated NaHCO3
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d792eee93daf4a1d8ae90318403cac22
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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